1-(3-溴苯基)-3-(二甲基氨基)-2-丙烯-1-酮 | 1203648-40-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 1-(3-溴苯基)-3-(二甲基氨基)-2-丙烯-1-酮
• 中文别名: 反-1-(3-溴苯基)-3-二甲氨基-2-丙烯-1-酮
• 英文名称: 1-(3-bromophenyl)-3-dimethylamino-2-propen-1-one
• 英文别名: (E)-1-(3-bromophenyl)-3-(dimethylamino)prop-2-en-1-one；(E)-1-(3-bromophenyl)-3-dimethylaminopropen-1-one；(E)-1-(3-bromo-phenyl)-3-dimethylamino-propenone；1-(3-bromo-phenyl)-3-dimethylamino-propenone；1-(3-Bromophenyl)-3-(dimethylamino)prop-2-en-1-one
• CAS: 1203648-40-1
• 化学式: C₁₁H₁₂BrNO
• 分子量: 254.126
• InChiKey: FBICCVMQKCGCST-VOTSOKGWSA-N

物化性质

• 熔点：
  67-69℃
• 沸点：
  320.6±42.0 °C(Predicted)
• 密度：
  1.355±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  14
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

安全信息

• 海关编码：
  2924299090

SDS

Material Safety Data Sheet

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Section 1. Identification of the substance
(E)-1-(3-Bromophenyl)-3-dimethylaminopropenone
Product Name:
Synonyms:

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Section 2. Hazards identification
Harmful by inhalation, in contact with skin, and if swallowed.
H315: Causes skin irritation
H319: Causes serious eye irritation
H335: May cause respiratory irritation
P261: Avoid breathing dust/fume/gas/mist/vapours/spray
Wear protective gloves/protective clothing/eye protection/face protection
P280:
P305+P351+P338: IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses if present
and easy to do – continue rinsing
P304+P340: IF INHALED: Remove victim to fresh air and keep at rest in a position comfortable for breathing
P405: Store locked up

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Section 3. Composition/information on ingredients.
(E)-1-(3-Bromophenyl)-3-dimethylaminopropenone
Ingredient name:
CAS number: 1203648-40-1

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Section 4. First aid measures
Immediately wash skin with copious amounts of water for at least 15 minutes while removing
Skin contact:
contaminated clothing and shoes. If irritation persists, seek medical attention.
Eye contact: Immediately wash skin with copious amounts of water for at least 15 minutes. Assure adequate
flushing of the eyes by separating the eyelids with fingers. If irritation persists, seek medical
attention.
Inhalation: Remove to fresh air. In severe cases or if symptoms persist, seek medical attention.
Wash out mouth with copious amounts of water for at least 15 minutes. Seek medical attention.
Ingestion:

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Section 5. Fire fighting measures
In the event of a fire involving this material, alone or in combination with other materials, use dry
powder or carbon dioxide extinguishers. Protective clothing and self-contained breathing apparatus
should be worn.

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Section 6. Accidental release measures
Personal precautions: Wear suitable personal protective equipment which performs satisfactorily and meets local/state/national
standards.
Respiratory precaution: Wear approved mask/respirator
Hand precaution: Wear suitable gloves/gauntlets
Skin protection: Wear suitable protective clothing
Eye protection: Wear suitable eye protection
Methods for cleaning up: Mix with sand or similar inert absorbent material, sweep up and keep in a tightly closed container
for disposal. See section 12.
Environmental precautions: Do not allow material to enter drains or water courses.

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Section 7. Handling and storage
Handling: This product should be handled only by, or under the close supervision of, those properly qualified
in the handling and use of potentially hazardous chemicals, who should take into account the fire,
health and chemical hazard data given on this sheet.
Storage: Store in closed vessels, refrigerated.

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Section 8. Exposure Controls / Personal protection
Engineering Controls: Use only in a chemical fume hood.
Personal protective equipment: Wear laboratory clothing, chemical-resistant gloves and safety goggles.
General hydiene measures: Wash thoroughly after handling. Wash contaminated clothing before reuse.

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Section 9. Physical and chemical properties
Not specified
Appearance:
Boiling point: No data
Melting point: No data
Flash point: No data
Density: No data
Molecular formula: C11H12BrNO
Molecular weight: 254.1

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Section 10. Stability and reactivity
Conditions to avoid: Heat, flames and sparks.
Materials to avoid: Oxidizing agents.
Possible hazardous combustion products: Carbon monoxide, nitrogen oxides, hydrogen bromide.

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Section 11. Toxicological information
No data.

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Section 12. Ecological information
No data.

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Section 13. Disposal consideration
Arrange disposal as special waste, by licensed disposal company, in consultation with local waste
disposal authority, in accordance with national and regional regulations.

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Section 14. Transportation information
Non-harzardous for air and ground transportation.

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Section 15. Regulatory information
No chemicals in this material are subject to the reporting requirements of SARA Title III, Section
302, or have known CAS numbers that exceed the threshold reporting levels established by SARA
Title III, Section 313.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  1-(3-溴苯基)-3-(二甲基氨基)-2-丙烯-1-酮 在 hydrazine hydrate 、 sodium hydride 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 18.5h， 生成 3-(3-溴苯基)-1-甲基-1H-吡唑
  参考文献：
  名称：

  [EN] PYRIMIDINE PYRAZOLYL DERIVATIVES AND THEIR USE AS IRAK INHIBITORS
  [FR] DÉRIVÉS DE PYRAZOLYLE PYRIMIDINE ET LEUR UTILISATION COMME INHIBITEURS D'IRAK

  摘要：

  本发明提供了用于治疗癌症、类风湿性关节炎和其他疾病的化合物（II）的公式。

  公开号：

  WO2015106058A1
• 作为产物：
  描述：

  N,N-二甲基甲酰胺二甲基缩醛 、 3'-溴苯乙酮 反应 72.0h， 以89%的产率得到1-(3-溴苯基)-3-(二甲基氨基)-2-丙烯-1-酮
  参考文献：
  名称：

  基于伍德沃德试剂K且具有不同目标选择性的基于活动的蛋白质组分析探针

  摘要：

  伍德沃德试剂K（WRK）是一种反应性杂环化合物，已用于蛋白质化学中，以共价和非特异性方式标记亲核氨基酸（特别是组氨酸和半胱氨酸）上的蛋白质。我们已经开发了一组基于WRK的基于活性的探针，并显示出令人惊讶和出乎意料的是，这些探针对人类蛋白质组中的几种蛋白质具有相当的选择性。WRK衍生的探针在巨噬细胞迁移抑制因子（MIF）中显示出对催化N末端脯氨酸的独特反应性，可用于标记并（如果配备了荧光团）在活细胞中成像MIF活性。

  DOI：

  10.1002/anie.201602666

文献信息

• Rh(III)-Catalyzed Enaminone-Directed C–H Coupling with α-Diazo-α-phosphonoacetate for Reactivity Discovery: Fluoride-Mediated Dephosphonation for C–C Coupling Reactions
  作者：Chao Song、Chen Yang、Hua Zeng、Wenjing Zhang、Shan Guo、Jin Zhu

  DOI：10.1021/acs.orglett.8b01406

  日期：2018.7.6

  Rh(III)-catalyzed enaminone-directed C–H coupling with α-diazo-α-phosphonoacetate has been used for the identification of fluoride-mediated dephosphonation C–C coupling reactivity for the synthesis of 4-hydroxy-1-naphthoates. Intermolecular C–C coupling of α-phosphonoacetate and benzaldehyde for (E)-selective α,β-unsaturated ester synthesis has also been achieved.

  Rh（III）催化的与α-重氮-α-膦酰基乙酸酯结合的烯胺酮定向的C–H偶联已用于鉴定氟化物介导的膦酰基化的C–C偶联反应，用于合成4-羟基-1-萘甲酸酯。还实现了α-膦酰基乙酸酯和苯甲醛的分子间CC偶联，用于（E）-选择性α，β-不饱和酯的合成。
• A new approach for the synthesis of novel naphthoquinone chalcone hybrid compounds
  作者：Ha-Thanh Nguyen、Tuyet Anh Dang Thi、Phuong Hoang Thi、Giang Le-Nhat-Thuy、Quynh Giang Nguyen Thi、Anh Nguyen Tuan、Tu Anh Le Thi、Tuyen Van Nguyen

  DOI：10.1016/j.tetlet.2021.153337

  日期：2021.9

  A facile and efficient synthesis of novel naphthoquinone-based chalcone hybrids ( and ) the microwave-assisted one-pot three-component reactions of 2-substituted-1,4-naphthoquinones, ,-dimethylformamide dimethyl acetal (DMF-DMA), and acetophenone derivatives has been reported. Whereas the synthesis of hybrids proceeded a condensation, 1,4-addition, rotation, elimination, and [1,3]-H shift sequence

  新型萘醌基查尔酮杂化物的简便高效合成（和）2-取代-1,4-萘醌、,-二甲基甲酰胺二甲基缩醛（DMF-DMA）和苯乙酮的微波辅助一锅三组分反应衍生品已有报道。杂化物的合成是通过缩合、1,4-加成、旋转、消除和[1,3]-H移位顺序进行的，而杂化物的合成是通过包括缩合、1,4-加成、旋转、消除和[1,3]-H转移的三步顺序形成的。 -加成反应和消除反应。
• Metal-free TBAI-catalyzed oxidative Csp3S bond formation through Csp2Csp2 bond and S N bond cleavage: A new route to β-keto-Sulfones
  作者：Yucai Tang、Ying Chen、Hui Liu、Min Guo

  DOI：10.1016/j.tetlet.2018.09.005

  日期：2018.10

  oxidative conditions and the corresponding β-keto-sulfone compounds were obtained in moderate to good yields. Importantly, this transformation offered the first protocol for Csp3S bond formation by oxidative Csp2Csp2 bond cleavage in one step.

  已经开发了新颖的TBAI催化的容易获得的N，N-二甲基亚氨基酮与磺酰肼的自由基磺酰化，以提供官能化的β-酮砜。在目前的氧化条件下，各种官能团的耐受性良好，并且以中等至良好的产率获得了相应的β-酮砜化合物。重要的是，该转化为通过一步氧化Csp 2 Csp 2键的裂解形成Csp 3 S键提供了第一个方案。
• Sulfonamide/sulfamate switch with a series of piperazinylureido derivatives: Synthesis, kinetic and in silico evaluation as carbonic anhydrase isoforms I, II, IV, and IX inhibitors
  作者：Alessio Nocentini、Davide Moi、Alessandro Deplano、Sameh M. Osman、Zeid A. AlOthman、Gianfranco Balboni、Claudiu T. Supuran、Valentina Onnis

  DOI：10.1016/j.ejmech.2019.111896

  日期：2020.1

  anti-cancer zinc-binder CAIs such as SLC-0111 and S4 was carried out by including the urea outer nitrogen atom into a substituted piperazine ring reducing the linker flexibility. The derivatives were assessed for the inhibition of CA I, II and IV (off-target isoforms) and the tumor-associated CA IX (anticancer drug target). CA I and IV were not effectively inhibited, whereas many low nanomolar inhibitors were

  我们在这里报告与哌嗪基脲基氨基磺酸盐作为人（h）碳酸酐酶抑制剂的彻底的构效关系（SAR）（CA，EC 4.2.1.1）。通过将尿素外氮原子包含在取代的哌嗪环中，降低了连接子的柔性，对报道的抗癌锌结合剂CAI（例如SLC-0111和S4）的结构进行了SAR研究。评估衍生物对CA I，II和IV（脱靶同种型）和与肿瘤相关的CA IX（抗癌药物靶标）的抑制作用。CA I和IV没有得到有效抑制，而许多低纳摩尔抑制剂被证明抗CA II（KI的范围为1.0-705.5 nM）和IX（KI的范围为0.91-155.9 nM）。有趣的是，
• A Synthesis of Novel Pyrazolylthienopyrimidine Derivatives as IL-6/STAT3 Inhibitors
  作者：Sung Min Kim、Seung Woong Lee、Yang-Heon Song

  DOI：10.5012/bkcs.2014.35.9.2859

  日期：2014.9.20

  at the various conditions (catalyst, reaction temperature and solvent). When the same reaction was carried out in refluxing ethanol in the presence of 1 equiv HCl as a catalyst, 3Aa was obtained as a major product in optimum yield (65%, Table 1, entry 6) within 6 h. Next, as depicted in Table 2, the reaction of 1A with 2b-h Table 1. Optimization for the reaction of 1A with 2a

  白细胞介素 6 (IL-6) 作为与 TNF-α 和 IL-8 一起的促炎细胞因子，在炎症的诱导以及慢性炎症免疫反应的持续中起核心作用。并且，已经在几种疾病的炎症组织中发现了过量产生的 IL-6，例如类风湿性关节炎、牛皮癣、炎症性肠病、骨关节炎、多发性骨髓瘤，以及人类动脉粥样硬化斑块。IL-6 与其受体（IL-6R，一种配体结合的 80 kDa 糖蛋白链）结合并诱导信号转导糖蛋白 130 (gp130) 的同源二聚化，导致 Janus 激酶 (Jak)/信号转导器的激活和转录信号激活因子 3 (STAT3)。STAT3 在大多数肿瘤和癌症中也经常过度表达或持续激活，并且发现激活的 STAT3 可以抑制肿瘤免疫监视。因此，IL-6 刺激的 STAT3 激活通路的阻断可能是发现新药的有吸引力的治疗靶点，目前正在紧张研究中。另一方面，噻吩并嘧啶及其衍生物是一类最具生物活性的重要化合物，具有抗菌、